The thought of him leaving doesn't totally faze me. In fact, if I met him I would thank him for what he's accomplished and say good luck in Chicago. Rumors of him looking elsewhere make sense to me. Put yourself in his shoes for a minute. I guess once you've hit the pinnacle of your profession twice, complacency is bound to kick in. The chance to become a team president and advance your career in a new market with money to burn must be awfully tempting.
Considering the pros and cons, one of the bad things about being GM of the Red Sox is the intensity of the fanbase and media scrutiny—just ask Nomar Garciaparra.
No matter what, I think we can say Theo Epstein is the best GM in Red Sox history. Bottom line is that while he's made mistakes, he's won two World Series, and that puts him in a class all by himself. I'd say the top four GMs in team history are Epstein, Lou Gorman, Dan Duquette and Dick O'Connell.
Although Theo is the best GM the team has ever had, the Red Sox have the resources and front-office structure to not miss a beat. The team can plug in another intelligent general manager with great personnel judgment, a good balance between short- and long-term needs, a keen eye for trades and a desire to win, and the good times will keep on coming.
Think about it. John Henry has been everything Red Sox fans could want in an owner. He installed smart people in the front office, spent money to acquire top notch talent, turned the team into a cash cow and won the ultimate prize. Have you ever heard the saying, make chicken salad out of chicken poo?
That's precisely what the team has done with Fenway Park. Under his leadership, the Red Sox have become a well-oiled machine with a nearly bottomless pit of money to throw at any player they need. The scouting department is impressive and they have a pipeline to inexpensive talent coming up from the minors. Besides the Yankees, is any team is going to beat the Red Sox in a bidding war? Absolutely not.
Theo Epstein is a pretty good GM, but he is also very lucky. Many of his mistakes in personnel have been covered up by John Henry's money. It must be incredible when a lot of your mistakes don't really bite the team in the butt. The Red Sox's financial resources are like a life raft; they've bailed Theo out of bad decisions that would have crippled 28 out the 30 teams in pro baseball.
Let's look at some of the factors with Theo. He is/was very good at letting veterans leave at just the right time, but awful at picking replacements for them. Pedro Martinez was a shoulder injury waiting to happen. However, he was replaced by Matt Clement. Nomar Garciaparra's best days were behind him by the time he was traded, but the players after him haven't worked either.
Derek Lowe was let go and who did Epstein replace him with? Wade Miller. Jason Bay hasn't been that great with the Mets (.245 AVG .332 OBP .371 SLG .703 OPS in 195 games) but the guy Theo picked to replace his bat in the outfield (Mike Cameron) was a disaster. Theo wasn't GM when Johnny Damon left, but traded for Coco Crisp, who bombed like Gigli at the box office.
Shortstop has been a revolving door ever since Nomar was traded. In my eyes, this shows Theo's free-agent judgment is a mixed bag. Edgar Renteria was a mistake. Alex Gonzalez wasn't a good enough hitter in their eyes. Julio Lugo was another misfire. Jed Lowrie hits fairly well and plays decent defense, but he can't stay on the field. Marco Scutaro hasn't really made an impact—I guess you can say he's been the best of a bad lot, but that's not saying much.
Manny Ramirez forced Theo's hand in 2008 and engineered a trade to the Dodgers. It sucked to see him leave, but Jason Bay was a very nice Plan B. In 200 games with the Red Sox, Bay hit .274 with a .380 OBP .534 SLG and .915 OPS.
In terms of drafting and developing players, Theo's record is remarkable. Ever since 2003 (the year he became GM), the team has struck gold with Jonathan Papelbon, Dustin Pedroia, Jacoby Ellsbury, Daniel Bard, Jon Lester and Clay Buchholz. He was right to hang onto Kevin Youkilis and Manny Delcarmen. Youkilis has been amazing, and Delcarmen was a very good middle reliever for awhile.
In terms of trades, Theo's done a great job of hyping up prospects who couldn't play in the pros and dumping them on unsuspecting teams. A good example of this is the Jason Bay deal. Craig Hansen and Brandon Moss were pumped as Hall of Famers, and neither one of them was good enough to last in the pros.
Recently, Theo has done a good job of gathering trade chips to get impact players who helped the big-league team right away. Victor Martinez was a great replacement as Jason Varitek started to decline, and Adrian Gonzalez has been a stud franchise player so far.
No matter what happens, the Red Sox are in good shape. If Theo stays it's great—if he leaves, the team has the infrastructure to withstand his departure. It's crazy how much two World Series titles change your mentality. Before 2004, I would have panicked that the team was losing their best front-office guy.
Now I know they'll be okay.